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How to Make Difficult Career Decisions

I was working with a client, let’s call him Tom, who wanted to write a book. However, Tom could never bring himself to start it, let alone complete it. 

It wasn’t until he began digging into his thoughts that he realized something that completely changed how he viewed his career. 

As we dug into his past stories, he remembered his High School English teacher telling him he didn’t have what it took to be a writer. 

At the time, he was devastated, but he had forgotten this memory.

He didn’t want to acknowledge that this was the catalyst for his belief that he wasn’t good enough. He loved this teacher. 

His memories of his English teacher were positive until he began digging into his memories.

He believed his teacher had taught him the power of a good story. 

As we dug deeper into his beliefs, he uncovered his truth.

When Tom kept digging, he saw how this moment planted the seed for his insecurities.

He was finally being honest with himself. 

He saw how mean he had been to himself. He didn’t believe he was a good writer so he had to work harder. His expectations were so high that he would never reach them. He was perpetually unhappy with his level of effort.

Tom had been encouraging his inner bully to keep beating himself up. He thought it was helping him be more disciplined. 

This created a domino effect in his decisions. 

When he brought this rough memory to light, he saw how he was complicit in building this identity. It held him back from doing what he loved.

Now that he brought this inner gem out, he couldn’t put it back. 

This is where digging deeper gets a little harder, but it’s also where you can improve your lens. 

You have the opportunity to uncover how this belief has formatted your life. 

I asked him, “What if you believed you were a good writer?”  

“Then I would be happier?”

I smiled. 

“What evidence do you have that you are a good writer?”

“I’ve been published in magazines, co-wrote a book with a friend, published by dozens of blogs…

Then it hit him. 

“Wait. I am a good writer. I’m not a great writer, but I’m good. I know that.”

What mattered the most was how he viewed himself. 

He could see that he was a good writer. Not a great one, but a good one. 

The facts backed it up. He had been published in magazines and websites. He just needed to be willing to appreciate how far he had come as a writer. He knew he could improve, but that didn’t negate his talent.

When you no longer adhere to the negative belief, you can go in any direction you want. 

You are free to fly. You have the freedom to learn from the fear because it teaches you to appreciate the possibilities just a bit more than you did last week or the week before.


Tom was able to reframe how he thought of himself as a writer. 

He smiled at this little gem, polished it, and held it to the light. 

He saw how this story’s power over him. It dictated his decisions. Now this little gem helped him see how to rewrite his own internal story. 

We created ways for him to document his hard work and see it as something to celebrate instead of beating himself up over it.

Over many months…

He began to encourage himself. When he sat down to write, he would celebrate by smiling and playing with his dog for 5 minutes. 

When he sent out a new piece to a magazine or a popular blog, he would take his dog for a short walk to reward himself.

He became the parent to himself that he wished he had when he was a child.

These inner gems became guideposts to improve his inner voice and do what he loved to do. 

I’m pleased to report that Tom finished his book’s rough draft and hired a writing coach to help him get the story into shape, so he can send it to publishers or self-publish it. 

He is taking pride in all his hard work instead of beating himself up for giving in to his fear.


The true value of digging deep is understanding yourself just a little better. 

You become more comfortable in your own skin, which allows you to make better decisions.

It’s about creating a fun and structured way to dig into your mindset. Developing a better understanding of yourself so that you can make decisions that align with your values. 

You can have a life filled with less anxiety and more energy because you focus on the things that matter to you. 

You might be afraid of digging deep because there is a lot of pain there, but it does get easier. 

If you see a therapist, counselor or attend a group, these are all good routines and important to your success. You should continue to do them. I suggest you also work to understand the lens through which you make decisions. 

You can begin to uncover your beliefs and see how they support or hurt your ability to take advantage of the opportunities in your life. This is how you’ll get the most value out of your time.

I created the Decision-Maker Personality Assessment to help you see how you view decisions. 

I noticed that there are five main decision-making personality types. Each one has its strengths and weaknesses. 

Gaining a better awareness of how you make decisions will help you get better results in your career.

If you want to begin to take advantage of the right opportunities in business and life, start by understanding what you say “yes” to, what you say “no” to, and why.

A simple journal prompt to use…

  • What decisions did I make today?
  • Why did I make them the way that I did?

It’s important not to judge yourself. We all make mistakes, but this prompt is just to deepen your self-awareness

Keep in mind that avoiding making a decision is also a “no” because you aren’t taking action. 

It’s important to find a way to step back and understand what your inner voice is saying. Is your ego wanting you to say “No” because it’s afraid of failure? 

Your inner dialogue influences all your decisions.

Look at how you are being hooked by your expectations. 

Notice how they are influencing your choices. 

This awareness makes decisions so much easier. 

If you are afraid to write a book, you’ll be able to discover why. 

If you are afraid to quit your job and find something better, you get a deeper understanding of the reasons behind this fear. You’ll finally be able to step back and be honest with yourself. 

You’ll learn to check in with your head, heart, and gut so you make the best decision for your future self. That’s how your career becomes joyful. 


You can stop putting too much pressure on making the perfect decision. 

You can’t control the outcome, but you can control the inputs.

As you deepen your self-awareness, you can make better decisions based on your values instead of trying to figure out the best outcomes. 

You do this by building habits like reflecting on your decisions.

You make the best decision with the information that you have and then watch how it unfolds. Then you take time to reflect and adjust, so you can make better future decisions that align with your values. 

Life is about focusing your energy on the things that drive the most value for you. Allocate your energy to the highest-leverage activities. The things that deliver the most return on your time. 

This is how you build a great career.

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